It’s Tuesday, time for the anonymous mailbag. (Apologies for not doing the anonymous mailbag last Tuesday, but when I’m on vacation I’m going to start taking off the Tuesday mailbag because I’m working all the time otherwise and this way my wife is more likely to sleep with me because I’m spending more time with the family).
Big news, next weekend I will be in St. Louis watching the SEC basketball tournament from the best suite in the arena and you can be there with me thanks to the weekly sponsor of the anonymous mailbag, Ryan Kelley and the The Home Loan Expert.
They are drawing the suite — which you can win to share with 11 of your friends — for the SEC title game tomorrow. But you have to go here to register for free. So make sure you do that and I look forward to seeing a bunch of you in St. Louis next weekend.
Also, for our Outkick VIP members, we are having VIP events in Las Vegas for the NCAA Tourney and in New York City in April. Details will be posted on our message board so make sure and check that out.
Okay, here we go with the mailbag.
As always, send your questions to firstname.lastname@example.org, anonymity guaranteed.
“So I was at church one night for an activity that was being held there. It’s an older building that’s part of the church, and the bathrooms are just unisex single holers that you lock behind you.
So, I’m taking a leak, and I hear the door knob rattle. I guess it was old and not working right, because to my surprise the door opens while I have my dick in my hand. Even more surprising is that it’s the preacher’s wife! She says sorry, closes the door quickly and walks off with both of us clearly embarrassed. Our church has a relatively young preacher, and said wife is in her 30s and very hot.
The good news is that I was having a phenomenal dick day. I’m about average (maybe slightly above), but that day I looked huge…think dude in the locker room in Any Given Sunday. Anyway, later on that evening I ran into her again, and I didn’t want to leave things as awkward as they were…so I told her not to worry about it, accidents happen, that sort of thing. And then I apologized that she had to see that, and she absolutely floored me with her response…
“Oh don’t worry, I’ve got all sons, so between them and my husband I’m used to it. Well, maybe not quite as big as yours,” and she winks and walks off.
What the hell? Was she just trying to be cool, or did I just get hit on by the preacher’s wife? Note, I have absolutely no interest in smashing her because I really don’t want that on my permanent record…but how was I supposed to respond, and how am I supposed to act around her now?”
Wow, the preacher’s wife wants the pipe!
I can’t conceive of any other way to take this than she’s willing to bang you.
Maybe I’m wrong on this — or just thinking totally like a guy — so women out there can feel free to disabuse me of this notion, but if a married woman sees a married man’s penis and then compliments him on the size of his penis, while winking, you’ve basically just climbed aboard the train to bangtown in my mind.
Put it this way, how do you think the preacher would respond if he found out that his hot wife had accidentally seen another man in the congregation’s penis and then she complimented him on the size of his penis while winking? (While, incidentally, taking a shot at her husband’s dick — inexcusable — and her son’s dicks — excusable because they’re kids and their dicks aren’t fully grown and may one day be massive.)
Now in the preacher’s wife’s defense maybe, possibly, she was just trying to make light of an awkward situation and just made a joke she thought was funny and didn’t intend it to be sexual, but I’m just not buying that because you, as you stated previously, were having a great dick day. Plus, she didn’t need to add the last part about how big your dick was. Because saying she sees dicks all day is completely true and could be funny standing alone. My wife has me and three boys, she literally can’t escape dicks all day long either. Last night we were fighting swords in the house and my three year old pulls down his pants, puts the sword in front of his penis and starts swinging it around saying, “Look at my penis!”
He’s three and he’s already making dick jokes.
I honestly think he may be the Mozart of dick jokes, just a total child prodigy.
Plus, it’s not like you’re bragging here and claiming to have a Greg Oden dick, you’re saying you’ve got an average to slightly above average dick and your dick just came to play that day. Your dick was like Kobe Bryant when he went for 81, just out there impossible to defend and be stopped by anyone. You were the opposite of George in Seinfeld when Elaine walked in on him.
It’s honestly ashame you’re not single because then you’d be tearing through the single women in this congregation like a hot knife through butter. Because you know the preacher’s wife would talk and before long you’re just swimming in illicit pre-marital church sex.
I think you have to take it easy from this point forward because the preacher’s wife is probably going to try to bang you and you have the potential to bring the entire congregation, and both your lives, collapsing around you.
Final thought, how diabolical could this preacher’s wife have been? She knows the door doesn’t lock, right? What if she intentionally walked in on you, already wanting to bang you, and now wants to bang you even more because she saw your dick. What if she’s a closet meat peeper?
We need regular updates on these interactions going forward, honestly.
And maybe the hot preacher’s wife needs to guest answer the mailbag questions one week.
I am a married dad with 3 kids. I am also a work-from-home statistical programmer for a major company making $100+K salary. I love my life, my family and my job. I have received numerous promotions and accolades in the years I’ve been doing this job.
Just this weekend I got an email from my sponsor praising all the work I do with them, I forwarded this to my boss and he agreed and recommended me for a bonus in the form of points to our company catalog (kinda like Skymall, pretty sweet stuff).
The problem however is this, since I work from home my co-workers don’t know this, but I sit around all day watching TV and dicking around online and stuff. There is no way I’d be able to fill my 40 hours a week with actual work, our company doesn’t even have that much work. Other co-workers complain about how swamped they are and work 50+ hour weeks, and I often pick up their tasks just to have stuff to do. Once in a while there is a time-crunch and I put in an honest day’s work, but that feels like maybe once or twice a month. I feel like a shitty employee yet I’m lauded as a model employee. I can’t help being able to do my tasks efficiently as I certainly have more of a workload than my co-workers. Should I try and pick up even more work? If I do I’m worried that my job will come crashing down all around me. Suggestions?”
I’d keep doing exactly what you’re doing.
You make over $100k a year working from home, don’t have to work that hard, and are still the best in your department. In the event people start getting laid off at your job, they’re likely to lay off the people who are worse at their job and you’d keep yours so short of the company going bankrupt because everyone they employ is an idiot, I’m not sure what you’re risking here.
Unless there is a tangible job above yours that you’d like to attain — and based on your email it doesn’t sound like there is — why rock the boat at work and either get yourself slammed with additional work or get other people who aren’t as skilled as you fired?
This was my biggest issue with practicing law, I felt like you weren’t rewarded for being efficient, you had to just be there at the office for at least 12 hours a day no matter what. How many people reading the anonymous mailbag at work right now who get paid for working forty hours could do their entire jobs in twenty hours? That is, if you just buckled in and focused on getting your work done, how many of you could get Thursday and Friday off every week and only work three days a week? I think it’s a ton of people, but most companies incentivize you more to be present than they do to be efficient.
That’s never made sense to me.
I know I’m much more efficient working from home than I would be if I worked in an office setting and people were always interrupting me all day long. Do you know many meetings I have in a week? Ideally, none. Because at meetings you just sit around talking about the work you need to do instead of actually doing the work.
I’m still astounded by the number of people who email asking if I’d like to get coffee or a beer with them. Total strangers! I guess I should be flattered by this, but I’ve got a website to run, a daily three hour radio show to do, a new book I’m writing, and a daily Periscope/Facebook show. And that’s just for work. I’ve also got a wife, three kids ten and under, and all of those obligations.
I don’t have time to golf or watch TV right now. The last thing I want to do is meet more strangers I don’t already know for coffee or beer.
Back when I started working at Fox Sports I was asked if I’d like to bring Outkick to Fox and become an editor/executive at FoxSports.com too.
And I said no way.
Because that would have meant I would have had to move to LA and also because I knew what I was good at — cranking out original content as a writer, radio and TV host. The last thing I wanted to do was edit someone else’s work or try and manage an entire website while sitting in meetings all day. That’s why I’ve kept Outkick lean, I only want writers who can write their own articles and edit them too so that I don’t have to worry about them at all.
Time I spend working on other people’s work is time I don’t have to get my own work done.
My advice: keep doing exactly what you’re doing.
“So the wife and I were cleaning the basement recently and found a sex tape we made when we were in our early 20’s. We are mid-late 30’s now. I’m wondering if it’s weird that I want to watch it. She is totally against it but has not thrown it away. It’s still on the shelf where we found it. I would normally do what every guy would do and just watch it, the only problem is it was so long ago that it’s on an 8 mm tape so I’d have to get real creative. Question is, do I keep asking her or just trash it? The longer it sits there the more I want to watch it. If I trash it I’ll be over it.”
I think you have to watch it and jerk off to yourself. (And your younger wife.)
But don’t tell her you jerked off to her in her twenties or, God forbid, that she was better looking then. In fact, whenever you watch the video you need to say that you find her much more attractive now than you did back when you made the video and suggest that you make a new video because she’s so much better looking now.
Say this even if it isn’t true.
(Note: this could actually be true too, your wife might be better looking now than back then. My wife is in better shape now after three kids than she was before she had three kids. It’s uncanny, honestly. But she has time now to work out that she didn’t have when she worked full time. This is one of the great benefits of your wife staying home from work — that I never even thought about — if she likes to work out she’s probably going to get in incredible shape without a job to worry about. Honestly, at my kid’s school, all the moms show up to drop off or pick up the kids in yoga pants and they’re like an entire sorority of milfs. Except they’re all probably in better shape now than they were when they were 21. God Bless America. And milfs.).
“I’m in the midst of a divorce, should be final in June. I have 100% custody of my 17 yo and 15 yo daughters. I’m dating a beautiful lady, much better than I deserve. Saturday evening she came over for dinner. No big deal just a relaxed night at home.
Next thing you know we end up in my room and the magic happens. She leaves a couple hours later.
My daughters were asleep as far as I knew. On Sunday morning my 17 yo was mad. She wouldn’t speak to me. When she finally did speak, she said she couldn’t believe I had sex. I of course lied, I said that we were just talking and playing words with friends. It took me several minutes to convince her that it didn’t happen. I had to go as far as quoting the Bible and explain that I wouldn’t disrespect my children or Jesus by doing that. So, how fast am I going to hell? Should I just be honest? Obviously I’ve not mentioned this to the woman I’m dating as this activity will never happen again. Wise one please shed some light on this!”
Why was your 17 year old daughter daughter upset? Because you had sex with someone else before the divorce was final, because you had sex outside of marriage, because she has been holding out hope that you and her mom were going to get back together again and the sex helped to kill that fantasy or because you’re her dad and she’s a teenager and the idea of your parents having sex is creepy to any teenager?
I’d need the answer here to give a more complete answer.
Having said that, your daughters are 17 and 15. That’s pretty old to be upset about your dad having sex outside of marriage.
I mean, don’t get me wrong, if I had teenage daughters I’d want them to believe they were going straight to hell if they had premarital sex too, but I think quoting scripture to sell the fact that you didn’t have sex is a bit much. Especially when, you know, you did have sex. And probably, to be fair, will be having sex again with the woman you’re dating.
The more interesting detail of your email is that you have 100% custody. What happened with your ex-wife such that you, a dad, ended up with 100% custody of your two teenage daughters? That suggests your ex-wife has major issues. I’d bet those issues are driving your daughter’s being upset more than the sex.
Given the present situation I think you’re in a tough spot here because what you should do is sit down your daughters when the divorce goes final and say that now that the divorce is final you may date other women. And the truth is that occasionally you may have sex with those women too. (Do that many Christians really get divorced and then become virgins until they’re married again? This seems insanely strange to me. I mean, you’re already not a virgin and you’ve already broken the sacred vow that you’ll never leave your spouse forever. At that point, do you really think God is going to reward you for getting divorced and not sleeping with someone again until you get married again?)
And you should tell your daughters that your sex life is your business and not theirs.
But then this opens you up to a major mess because what if your girls say their sex life is their business too and start banging people like crazy over a misguided rebellion surrounding their dad’s divorce?
So I’d probably just keep lying for now.
And maybe schedule sex when the girls aren’t at home.
“I have been dating my girlfriend for almost two years. We graduated college within the past year and took jobs in different cities an hour away from each other. I think I love her, she is very hot and might want to marry her, but I also think she might be crazy. She is the only girl I’ve ever dated so I don’t have anyone to compare her craziness to. Some examples are:
I don’t know if all girls are crazy similar to her and I should just get used to it, or if she is extra crazy and I should know about it. I need you to tell me how crazy the average girl is please.”
All girls are crazy, especially if they are teenagers or in their twenties.
I think this is pretty average level crazy, honestly. The question you have to decide, as all men before you have too, is if she’s hot enough to put up with it.
The good news is, as they age women become less crazy. But they also become less good looking and less interested in sleeping with you too. So it’s kind of bittersweet, honestly.
“What would you do if your nice and kind wife chose not to lose weight after the birth of your children, and 12 years after the last child was born, is still 50-60 pounds overweight? In the interest of not breaking up your family, because you adore your children, would you consider having a long-term affair with someone who is also in an unhappy marriage?”
Does the other woman have a fat husband? If so, could her fat husband and your fat wife have an affair while you have an affair with his skinny wife?
Because what you’re really asking here is this — is it okay to cheat on your wife if she’s fat?
And the answer is, clearly, no.
You pledged to stay with your wife for better/skinny or worse/fat.
So you shouldn’t cheat on your wife. But if you are going to cheat on your wife, you also shouldn’t do it with another man’s wife because then there’s a decent chance that you don’t just break up your own marriage, but that you break up his and hers too.
This is why I think prostitution should be legal and not stigmatized. Because I bet you’d be fine staying married to your wife if you could pay to bang one different prostitute every month, wouldn’t you?
That way you’d pay for sex, which is, in my opinion, just a service like a chef preparing you a meal or a personal trainer helping you work out, and you wouldn’t break up your own or anyone else’s marriage, keeping both sets of children in relatively stable two parent households.
The questions this week were fabulous. Send your own to email@example.com, anonymity guaranteed.